Method for combating soil insects and termites

ABSTRACT

THIS INVENTION RELATES TO A METHOD OF COMBATING SOIL INSECTS AND TERMITES WITH PREPARATION CONTAINING AS THE ACTIVE INGREDIENT A CARBAMATE OF THE GENERAL FORMULA   (R1-N(-R2)-COO-),R,X1,X2-BENZENE   IN WHICH R1 AND R2 REPRESENT HYDROGENS OR AN ALIPHATIC GROUP X1 AND X2 REPRESENT HYDROGEN, HALOGEN, AN ALIPHATIC OR NITRO GROUP, AND R IS THE ORTHO- OR META-POSITION TO THE CARBAMYLOXY GROUP REPRESENTS AN ALDEHYDE GROUP WHICH IS ACETALIZED AND/OR THIOALCOHOLS, PREFERABLY TO FORM A HETEROCYCLIC RING CONTAINING OXYGEN AND/OR SULFUR ATOMS.

United M 1 METHOD FOR COMBATING SOIL INSECTS AND TERMITES .Fritz Bachmann, Riehen, Switzerland, assignor to Ciba I Limited, Basel, Switzerland No Drawing. Filed Nov. 21, 1968, Ser. No. 777,906 Claims priority, application Switzerland, Nov. 24, 1967, 16,530/67 Int. Cl. A01n 9/28 US. Cl. 424-278 1 Claim ABSTRACT OF THE DISCLOSURE v The invention relates to a method of combating soil insects and termites with preparations containing as the active ingredient a carbamate of the general formula in which R, and R represent hydrogen or an aliphatic group; X and X represent hydrogen, halogen, an aliphatic or nitro group", and R'is' the orthoor meta-position to the carbamyloxygroup represents an aldehyde group which is acetalized with alcohols and/or thioalcohols, preferably to form a heterocyclic ring containing oxygen and/ or sulfur atoms.

It is known that the compounds of the formula may be used as active ingredients in pesticidal preparations. 'In this formula R and R;,, which may be identical or different, each represents a hydrogen atom or a lower alkyl or alkenyl group, X and X which may be identical or diiferent, each represents a hydrogen atom, a lower saturated or unsaturated aliphatic group, a halogen atom or a nitro group, and R represents a grouping of the formula H in orthoor meta-position to the carbamyloxy group, wherein X and X, may be identical or different and each represents an oxygen or a sulphur atom, R and R may be identical or dilferent and each represents an alkyl, alkenyl or alkinyl group, or together with the whole grouping R may form a saturated or unsaturated heterocycle with 5 to 7 members whichcontains X and X, as hetero atoms, and R and R may be substituted by lower aliphatic groups, by halogen atoms, or nitro or hydroxyl groups. These compounds possess valuable biocidal, especially insecticidal and acaricidal properties. Furthermore, they also possess bactericidal, fungicidal and molluscicidal properties. These carbamates are especially active against pests found in storerooms and against insects that damage plants, for example, aphids and prodenia.

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The present invention is based on the surprising observation that the active substances defined by the general Formula I display a strong activity against soil insects and termites.

In order to control soil insects, the active substances of the Formula I may be used in one of the usual formulations described in detail in Dutch Auslegeschrift No. 3,5 13,024.

Quite generally, growing plants or plants shortly before their ripening may be treated with an aqueous dispersion, or an aqueous dispersion of one of the active substances may be poured over the soil before seeding or planting it, or the active substance as such may be worked into the soil by one of the conventional mechanical methods.

Termites are the most widely encountered animal pests damaging materials in warm climates. In contrast to other pests, they destroy not only materials on which they feed, that is to say cellulosic substances, but also a wide variety of other materials of diverse chemical compositions. Thus, apart from timber, paper and textiles, termites attack also plastics, rubber, lacquers, leather, bitumen and cement compositions and damage them. Even the smallest amount of damage caused by eating termites may have an extremely serious effect because having been attacked in this manner, for example, electric gear, cables or machine parts may be left completely useless.

Since it is not feasible to combat the termites directly, the safest way to prevent destruction of the technical appliances is protect the materials from termite damage. In this connection, not only the contact eifect but also the gas phase effect of the active substances of this invention can be utilised.

At the present stage, with the use of suitable substances and methods, it is also possible to protect non-textile materials against termite damage by impregnating them with the active substances of the Formula I, or by incorporating such active substances with the starting materials. Such a treatment is not necessarily intended to destroy the pests, but at the same time it may render the materials resistant to them.

Anti-termite substances must satisfy various special requirements. Inter alia, for example, they must withstand the heat-treatment required in the manufacture and processing of the non-textile materials to be protected, and they must be stable towards extraneous substances, for example, plastizers or foaming agents without affecting the anti-termite protection. Moreover, the preparations must permanently protect the materials concerned and remain stable even in tropical climate. They must not affect the quality and properties of the materials concerned and finally they must be physiologically acceptable to both humans and farm animals.

The active substances of the Formula I satisfy all these conditions.

Accordingly, the present invention is concerned with the use of the carbamates of the general formula for controlling soil insects and termites. In this formula R and R may be identical or dilferent and each represents hydrogen, a lower alkyl or alkenyl group; X and X may be identical or different and each represents hydrogen or a lower saturated or unsaturated aliphatic group, a halogen atom or a nitro group, and R represents a grouping of the formula which is in orthoor meta-position to the carbamyloxy group; X and X, may be identical or different and each represents an oxygen or sulphur atom; R and R may be identical or different and each represents an alkyl, alkenyl or alkinyl group or together with the whole group R may form a saturated or unsaturated heterocycle having 5 to 7 members which contains X and X; as hetero atoms, and R and R may be substituted by lower aliphatic groups, halogen, a nitro or hydroxyl group. The carbamates may be used with an appropriate vehicle and optionally in admixture with other known agents suitable for combating soil insects and/ or termites.

The lower alkyl, alkenyl and alkinyl groups indicated above for R X and X usually contain 1 to 4 carbon atoms. The lower aliphatic groups, which are possible substituents for R and R usually contain 1 to 4 carbon atoms and are preferably corresponding alkyl groups which may be interrupted by hetero atoms, for example, oxygen, sulphur or nitrogen or substituted as indicated for R and R Especially preferred are compounds in which R X and X each represents hydrogen, R represents a methyl group and R and R are linked together so that R becomes a 5- to 7-membered, especially S-membered, heterocycle in which X and X each represents sulphur and/ or oxygen, preferably oxygen.

Accordingly, the following compounds are especially valuable:

C0 liHCH O C0 NHCH EXAMPLE 1 (a) Controlling the cabbage-root fly [Phorbia brassicae Bouch].

Cauliflower was planted on May 2. On May 8, 100 cc. of an 0.05% aqueous solution of wettable powder prepared from the active substance of the formula (A) o cu cs H I was poured over each plant.

Evaluation ywas carried out on June by counting the live maggots, and the damage caused to the (washed) roots was designated by the values 0 to 5.

The following results were obtained:

Num-

Number Damage grouping in percent her of mag- Treatment plants 0 1 2 3 4 5 gets None 36 3 47 47 3 30 0.05% solution of aet tive substance (11).- 36 36 53 11 0 (b) White cabbage was planted on July 7. On July 14, cc. of active substance A (see under (a) above) was poured over each cabbage plant. Evaluation was carried out on August 15 as described'under (a) above.

(a) Controlling the turnip root fly [Phorb ia floralis Fallen].

When the root of the radish variety Ostergruss was beginning to thicken on July 26, the soil was treated with" 2 litres per square metre of an 0.05% aqueous solution I of the active substance A. Evaluation was carried out on August 24 by counting the infestation found on each of 20 radishes.

Percent infestationuntreated 70 Percent eifect0.05% WP 50 substance A 100 0.1% diazinoneEC 25 79 (b) The procedure used in another test was as described under (a) above. The treatment was carried out on August 29, the evaluation on September 25, by- I checking the infestation on 50 (untreated 100) radishes.

The following results were obtained:

Percent infestation-untreated 72 Percent effect0.05% A WP 50 83 EXAMPLE 3 Combating white grubs [Larvae of Melolamha melolontha L].

Shortly before earthing up the potatoes in a potato field, plots of 5 square metre each were parcelled off; according to the block variation, in 4 repetitions. The preparations were applied in an amount of 2 litres per square metre, equal to 5 kg. of active substance per hectare.

On September 7, the potatoes were lifted and inspected for damage by white grubs. The grubs were in the second larval state.

The following results were obtained:

In percent In percent 7 Damaged tubers numbers weight Untreated 7. 5 10 Active substance A- 2. 7 1. 5

Aldrin 2. 2 V 1. 3

EXAMPLE 4 Combating termites [Kalotermes flaviC0llis], The active substance of the formula was applied in an amount of 2 g. per square metre to 7 pieces of pine wood 20 x 20 1:5 mm., and 3 weeks later. the examination was carried out.

In the force and repellency tests, the untreated control samples were extensively damaged.

The samples treated with the substance (B) displayed a repellant and toxic activity. No damage caused by termites was detectable.

Damage within 30 days Toxicity Repel- Repel- Sample Force lency Force lency Toxicity Untreated Normal Normal 90. Compound (B). 0 Toxic Toxic Repellant effect: percent termites Sample removed from sample- Untreated 2.6 Compound (B) -2 100 EXAMPLE Combating elateridae larvae [wire 'worms].

The tests were made in block variation with 3 repetitions on plots of 25 square metres each. The soil was sprayed with 400 litres per hectare and respectively sprinkled with granulate and then slightly worked over. A few days later, rows of maize were seeded. When the emerging plants had reached a height of at least cm., the number of plants, except in thc'region of the edges, in each plot was counted. Infestation by wire worms reduces the number of plants.

Varieties tested: Donja Kupina (DK) and Veleevac Location of test: Jugoslavia Seeding date: (V)Apr. 30, 1968 (DK)-May 11, 1968 Results (application of all preparations in an amount of 5 kg. per hectare):

Relative number of plants DK on V on Preparation June 28 June 29 Untreated 10;) 121 104 6 127 109 Endosulian WP 35 115 Bromophos sprinkling agent 98 The abbreviations used in the example mean:

EC 25 =emulsion concentrate containing 25% of an active ingredient, WP 50=wettable powder containing 50% of an active ingredient, G 6=granulates containing 6% of an active ingredient.

I claim: 1. A method for combating soil insects, which comprises fapplyingto the soil site to be treated a soil insecticidal amount of the compound of the formula V. D. TURNER, Assistant Examiner US. Cl. X.R. 424-276, 277, 300 

